IE52508B1 - 3,1-benzoxazin-2-ones,the preparation and use thereof - Google Patents

3,1-benzoxazin-2-ones,the preparation and use thereof

Info

Publication number: IE52508B1
Authority: IE; Ireland
Prior art keywords: group; salt; alkyl; hydrogen; methyl
Prior art date: 1980-07-12

Application number

IE1567/81A

Other languages

English (en)

Other versions

IE811567L (en

Original Assignee

Boehringer Ingelheim Int

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1980-07-12

Filing date

1981-07-10

Publication date

1987-11-25

1981-07-10 Application filed by Boehringer Ingelheim Int filed Critical Boehringer Ingelheim Int

1982-01-12 Publication of IE811567L publication Critical patent/IE811567L/xx

1987-11-25 Publication of IE52508B1 publication Critical patent/IE52508B1/en

Links

238000002360 preparation method Methods 0.000 title claims abstract description 9
150000003839 salts Chemical class 0.000 claims abstract description 153
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 140
150000001875 compounds Chemical class 0.000 claims abstract description 78
238000000034 method Methods 0.000 claims abstract description 32
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 26
239000002253 acid Substances 0.000 claims abstract description 24
229910052801 chlorine Inorganic materials 0.000 claims abstract description 20
239000001257 hydrogen Substances 0.000 claims abstract description 19
-1 hydroxy, methyl Chemical group 0.000 claims abstract description 19
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 17
229910052731 fluorine Inorganic materials 0.000 claims abstract description 15
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 13
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 12
239000011737 fluorine Substances 0.000 claims abstract description 12
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
230000003195 tocolytic effect Effects 0.000 claims abstract description 7
230000001077 hypotensive effect Effects 0.000 claims abstract description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 5
208000001953 Hypotension Diseases 0.000 claims abstract description 4
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 4
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims abstract description 4
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 4
208000021822 hypotensive Diseases 0.000 claims abstract description 4
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims abstract 2
125000000217 alkyl group Chemical group 0.000 claims description 23
239000000460 chlorine Substances 0.000 claims description 12
230000000747 cardiac effect Effects 0.000 claims description 8
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 6
125000006239 protecting group Chemical group 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
230000001813 broncholytic effect Effects 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
241001465754 Metazoa Species 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
229940124630 bronchodilator Drugs 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 4
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
101100240517 Caenorhabditis elegans nhr-11 gene Proteins 0.000 claims 1
239000000969 carrier Substances 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 abstract description 6
230000000144 pharmacologic effect Effects 0.000 abstract description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 4
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
125000001153 fluoro group Chemical group F* 0.000 abstract 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 36
239000002585 base Substances 0.000 description 35
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 30
FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical compound C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 0.000 description 28
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 22
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 16
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
ALYNCZNDIQEVRV-UHFFFAOYSA-M 4-aminobenzoate Chemical compound NC1=CC=C(C([O-])=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-M 0.000 description 11
239000000203 mixture Substances 0.000 description 11
239000000243 solution Substances 0.000 description 11
239000003054 catalyst Substances 0.000 description 9
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
239000013543 active substance Substances 0.000 description 7
230000036772 blood pressure Effects 0.000 description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
239000000126 substance Substances 0.000 description 6
241000700159 Rattus Species 0.000 description 5
239000002775 capsule Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
229910052697 platinum Inorganic materials 0.000 description 4
229910000033 sodium borohydride Inorganic materials 0.000 description 4
239000012279 sodium borohydride Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
235000011114 ammonium hydroxide Nutrition 0.000 description 3
238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
239000012153 distilled water Substances 0.000 description 3
230000002045 lasting effect Effects 0.000 description 3
229910052759 nickel Inorganic materials 0.000 description 3
238000006722 reduction reaction Methods 0.000 description 3
GZOJTRITAZODJV-UHFFFAOYSA-N 3,1-benzoxazin-2-one Chemical class C1=CC=CC2=COC(=O)N=C21 GZOJTRITAZODJV-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
206010010356 Congenital anomaly Diseases 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
239000001828 Gelatine Substances 0.000 description 2
239000007818 Grignard reagent Substances 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
206010020772 Hypertension Diseases 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
208000036029 Uterine contractions during pregnancy Diseases 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 2
239000002220 antihypertensive agent Substances 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
150000004795 grignard reagents Chemical class 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
239000008101 lactose Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000011976 maleic acid Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 2
229910003446 platinum oxide Inorganic materials 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000007127 saponification reaction Methods 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000000600 sorbitol Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
229940086735 succinate Drugs 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
229930008281 A03AD01 - Papaverine Natural products 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
VYWQTJWGWLKBQA-UHFFFAOYSA-N [amino(hydroxy)methylidene]azanium;chloride Chemical compound Cl.NC(N)=O VYWQTJWGWLKBQA-UHFFFAOYSA-N 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
150000001414 amino alcohols Chemical class 0.000 description 1
229940064734 aminobenzoate Drugs 0.000 description 1
229960004050 aminobenzoic acid Drugs 0.000 description 1
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
239000000043 antiallergic agent Substances 0.000 description 1
229940030600 antihypertensive agent Drugs 0.000 description 1
239000002249 anxiolytic agent Substances 0.000 description 1
210000000709 aorta Anatomy 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000037396 body weight Effects 0.000 description 1
OJGDCBLYJGHCIH-UHFFFAOYSA-N bromhexine Chemical compound C1CCCCC1N(C)CC1=CC(Br)=CC(Br)=C1N OJGDCBLYJGHCIH-UHFFFAOYSA-N 0.000 description 1
229960003870 bromhexine Drugs 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical class BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 1
239000002371 cardiac agent Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
239000000812 cholinergic antagonist Substances 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
238000001816 cooling Methods 0.000 description 1
101150102059 cry3Aa gene Proteins 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
150000002373 hemiacetals Chemical class 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
229910052740 iodine Chemical group 0.000 description 1
229960001361 ipratropium bromide Drugs 0.000 description 1
KEWHKYJURDBRMN-ZEODDXGYSA-M ipratropium bromide hydrate Chemical compound O.[Br-].O([C@H]1C[C@H]2CC[C@@H](C1)[N@@+]2(C)C(C)C)C(=O)C(CO)C1=CC=CC=C1 KEWHKYJURDBRMN-ZEODDXGYSA-M 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000005259 measurement Methods 0.000 description 1
MPLHCFBMCCBBKT-UHFFFAOYSA-N methyl 2-hydroxy-5-oxaldehydoylbenzoate Chemical compound COC(=O)C1=CC(C(=O)C=O)=CC=C1O MPLHCFBMCCBBKT-UHFFFAOYSA-N 0.000 description 1
YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 1
230000003170 musculotropic effect Effects 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
GTDQGKWDWVUKTI-UHFFFAOYSA-N o-aminoacetophenone Chemical class CC(=O)C1=CC=CC=C1N GTDQGKWDWVUKTI-UHFFFAOYSA-N 0.000 description 1
229960001789 papaverine Drugs 0.000 description 1
230000002445 parasympatholytic effect Effects 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000005932 reductive alkylation reaction Methods 0.000 description 1
230000000894 saliuretic effect Effects 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
230000002048 spasmolytic effect Effects 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229940125712 tocolytic agent Drugs 0.000 description 1
239000003675 tocolytic agent Substances 0.000 description 1
230000000304 vasodilatating effect Effects 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/18—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 2
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Endocrinology (AREA)
Reproductive Health (AREA)
Pulmonology (AREA)
Urology & Nephrology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

IE1567/81A 1980-07-12 1981-07-10 3,1-benzoxazin-2-ones,the preparation and use thereof IE52508B1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19803026534 DE3026534A1 (de)	1980-07-12	1980-07-12	3,1-benzoxazin-2-one, ihre herstellung und verwendung

Publications (2)

Publication Number	Publication Date
IE811567L IE811567L (en)	1982-01-12
IE52508B1 true IE52508B1 (en)	1987-11-25

Family

ID=6107085

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IE1567/81A IE52508B1 (en)	1980-07-12	1981-07-10	3,1-benzoxazin-2-ones,the preparation and use thereof

Country Status (25)

Country	Link
US (1)	US4341778A (es)
EP (1)	EP0043940B1 (es)
JP (1)	JPS5748975A (es)
KR (1)	KR850000755B1 (es)
AT (1)	ATE9336T1 (es)
AU (1)	AU540916B2 (es)
CA (1)	CA1165317A (es)
DD (1)	DD202018A5 (es)
DE (2)	DE3026534A1 (es)
DK (1)	DK149851C (es)
ES (4)	ES8205402A1 (es)
FI (1)	FI74703C (es)
GB (1)	GB2080296B (es)
GR (1)	GR74333B (es)
HK (1)	HK98286A (es)
HU (1)	HU183515B (es)
IE (1)	IE52508B1 (es)
IL (1)	IL63285A (es)
NO (1)	NO158578C (es)
NZ (1)	NZ197678A (es)
PH (1)	PH17425A (es)
PT (1)	PT73338B (es)
SG (1)	SG77686G (es)
YU (1)	YU170181A (es)
ZA (1)	ZA814687B (es)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4446319A (en) *	1981-04-28	1984-05-01	Takeda Chemical Industries, Ltd.	Aminocyclitols and their production
JPS62238288A (ja) *	1986-04-04	1987-10-19	Nippon Tokushu Noyaku Seizo Kk	環状カルバメ−ト及び農園芸用殺菌剤
FR2636065B1 (fr) *	1988-09-08	1993-05-07	Fabre Sa Pierre	Nouveaux derives de dihydro-2,3 arylacoylaminoalcoyl-3 4h-benzoxazine-1,3 ones-4, leur preparation et leur application en tant que medicaments utiles en therapeutique
JP2807577B2 (ja) *	1990-06-15	1998-10-08	エーザイ株式会社	環状アミド誘導体
FR2680172B1 (fr) *	1991-08-05	1993-11-19	Fabre Medicament Pierre	Nouvelles piperazinylalcoyl-3 dihydro-2,3 4h-benzoxazine-1,3 ones-4 substituees, leur preparation et leur application en therapeutique.
CA2210138A1 (en) *	1995-01-24	1996-08-01	Peter D. Williams	Tocolytic oxytocin receptor antagonists
US5874430A (en) *	1996-10-02	1999-02-23	Dupont Pharmaceuticals Company	4,4-disubstitued-1,4-dihydro-2H-3,1-benzoxazin-2-ones useful as HIV reverse transcriptase inhibitors and intermediates and processes for making the same
DE102004003428A1 (de) *	2004-01-23	2005-08-11	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Neue langwirksame Beta-2-Agonisten, und deren Verwendung als Arzneimittel
EP1844768A1 (en) *	2005-01-19	2007-10-17	Dainippon Sumitomo Pharma Co., Ltd.	Aromatic sulfone compound as aldosterone receptor modulator
DE102005008921A1 (de) *	2005-02-24	2006-08-31	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Neue Arzneimittel zur Behandlung von Atemwegserkrankungen
US7423146B2 (en)	2005-11-09	2008-09-09	Boehringer Ingelheim International Gmbh	Process for the manufacturing of pharmaceutically active 3,1-benzoxazine-2-ones
PE20080425A1 (es) *	2006-08-22	2008-06-16	Boehringer Ingelheim Int	Formulacion aerosol para la inhalacion de beta-agonistas
UY30550A1 (es) *	2006-08-22	2008-03-31	Boehringer Ingelheim Int	Nuevos beta-agonistas enantioméricamente puros, procedimientos para su preparacion y su uso como medicamentos
EP2056836A1 (en) *	2006-08-22	2009-05-13	Boehringer Ingelheim International GmbH	Powder formulations for inhalation containing enantiomerically pure beta-agonists
PE20081358A1 (es) *	2006-08-22	2008-10-31	Boehringer Ingelheim Int	Combinaciones farmacologicas para el tratamiento de enfermedades de la vias aereas
EP2093219A1 (de)	2008-02-22	2009-08-26	Boehringer Ingelheim International Gmbh	Kristalline, enantiomerenreine Salzform eines Betamimetikums und dessen Verwendung als Arzneimittel

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3526621A (en) *	1966-08-03	1970-09-01	Farmaceutical Italia Soc	Substituted 3,1-benzoxazin-2-one
DE2609645A1 (de) *	1976-03-09	1977-09-15	Boehringer Sohn Ingelheim	Aminoalkylheterocyclen
US4163053A (en) *	1977-12-27	1979-07-31	Schering Corporation	Anti-hypertensive 5-[2-(substituted anilinoalkylamino)-1-hydroxyalkyl]salicylamides
DD144050A5 (de) *	1978-06-05	1980-09-24	Ciba Geigy Ag	Verfahren zur herstellung von n-alkylierten aminoalkoholen
DE2833140A1 (de) *	1978-07-28	1980-02-07	Boehringer Sohn Ingelheim	Neue n-substituierte heterocyclen

1980
- 1980-07-12 DE DE19803026534 patent/DE3026534A1/de not_active Withdrawn
1981
- 1981-06-22 DE DE8181104787T patent/DE3166003D1/de not_active Expired
- 1981-06-22 AT AT81104787T patent/ATE9336T1/de not_active IP Right Cessation
- 1981-06-22 EP EP81104787A patent/EP0043940B1/de not_active Expired
- 1981-07-06 US US06/280,349 patent/US4341778A/en not_active Expired - Fee Related
- 1981-07-07 PH PH25873A patent/PH17425A/en unknown
- 1981-07-09 PT PT73338A patent/PT73338B/pt unknown
- 1981-07-09 YU YU01701/81A patent/YU170181A/xx unknown
- 1981-07-10 NO NO812355A patent/NO158578C/no unknown
- 1981-07-10 ES ES503837A patent/ES8205402A1/es not_active Expired
- 1981-07-10 NZ NZ197678A patent/NZ197678A/en unknown
- 1981-07-10 FI FI812183A patent/FI74703C/fi not_active IP Right Cessation
- 1981-07-10 GB GB8121321A patent/GB2080296B/en not_active Expired
- 1981-07-10 CA CA000381559A patent/CA1165317A/en not_active Expired
- 1981-07-10 DK DK306781A patent/DK149851C/da not_active IP Right Cessation
- 1981-07-10 ZA ZA814687A patent/ZA814687B/xx unknown
- 1981-07-10 IE IE1567/81A patent/IE52508B1/en unknown
- 1981-07-10 IL IL63285A patent/IL63285A/xx unknown
- 1981-07-10 DD DD81231670A patent/DD202018A5/de unknown
- 1981-07-10 GR GR65470A patent/GR74333B/el unknown
- 1981-07-10 HU HU812036A patent/HU183515B/hu unknown
- 1981-07-10 AU AU72731/81A patent/AU540916B2/en not_active Ceased
- 1981-07-11 KR KR8102523A patent/KR850000755B1/ko not_active Expired
- 1981-07-13 JP JP56109186A patent/JPS5748975A/ja active Pending
1982
- 1982-01-12 ES ES508653A patent/ES508653A0/es active Granted
- 1982-01-12 ES ES508654A patent/ES508654A0/es active Granted
- 1982-01-12 ES ES508655A patent/ES8300727A1/es not_active Expired
1986
- 1986-09-26 SG SG776/86A patent/SG77686G/en unknown
- 1986-12-18 HK HK982/86A patent/HK98286A/xx unknown

Also Published As

Publication number	Publication date
JPS5748975A (en)	1982-03-20
PT73338A (de)	1981-08-01
KR830006248A (ko)	1983-09-20
FI812183L (fi)	1982-01-13
YU170181A (en)	1983-10-31
GB2080296A (en)	1982-02-03
HU183515B (en)	1984-05-28
AU540916B2 (en)	1984-12-06
ES508655A0 (es)	1982-11-01
DD202018A5 (de)	1983-08-24
PT73338B (en)	1983-06-20
IL63285A (en)	1985-03-31
ES8300727A1 (es)	1982-11-01
IL63285A0 (en)	1981-10-30
HK98286A (en)	1986-12-24
FI74703C (fi)	1988-03-10
IE811567L (en)	1982-01-12
GR74333B (es)	1984-06-25
DE3166003D1 (en)	1984-10-18
DE3026534A1 (de)	1982-03-18
CA1165317A (en)	1984-04-10
NZ197678A (en)	1984-12-14
KR850000755B1 (en)	1985-05-25
ES8300726A1 (es)	1982-11-01
DK149851C (da)	1987-05-04
DK149851B (da)	1986-10-13
FI74703B (fi)	1987-11-30
GB2080296B (en)	1983-09-28
US4341778A (en)	1982-07-27
NO158578B (no)	1988-06-27
ZA814687B (en)	1983-03-30
ES8300725A1 (es)	1982-11-01
EP0043940B1 (de)	1984-09-12
DK306781A (da)	1982-01-13
PH17425A (en)	1984-08-08
ES508653A0 (es)	1982-11-01
NO812355L (no)	1982-01-13
ES508654A0 (es)	1982-11-01
EP0043940A1 (de)	1982-01-20
AU7273181A (en)	1982-09-16
ATE9336T1 (de)	1984-09-15
ES503837A0 (es)	1982-06-01
SG77686G (en)	1987-02-27
NO158578C (no)	1988-10-05
ES8205402A1 (es)	1982-06-01

Publication	Publication Date	Title
IE52508B1 (en)	1987-11-25	3,1-benzoxazin-2-ones,the preparation and use thereof
US4042700A (en)	1977-08-16	Quaternary N-β-substituted N-alkyl-nortropine benzilates
KR910009937B1 (ko)	1991-12-06	피페리딘 유도체 및 그의 제법
AU635369B2 (en)	1993-03-18	New (1-naphtyl)piperazine derivatives, process for preparing these and pharmaceutical compositions containing them
EA011407B1 (ru)	2009-02-27	Гидраты и полиморфы 4-[[(7r)-8-циклопентил-7-этил-5,6,7,8-тетрагидро-5-метил-6-оксо-2-птеридинил]амино]-3-метокси-n-(1-метил-4-пиперидинил)бензамида, способы их получения и их применение в качестве лекарственных средств
JPH02243688A (ja)	1990-09-27	新規キヌクリジン類、該化合物を含有する医薬組成物、及びその製造方法
JPH06340620A (ja)	1994-12-13	新規なアミノピペリジン、アミノピロリジンおよびアミノパーヒドロアゼピン化合物
FI63225C (fi)	1983-05-10	Foerfarande foer framstaellning av farmakologiskt vaerdefulla isokinolin-1-oner eller bensazepin-1-oner
US3804849A (en)	1974-04-16	2-amino-4,5,7,8-tetrahydro-6h-thiazolo or oxazolo(5,4-d)azepines and salts
US4145427A (en)	1979-03-20	N- 1-(3-Benzoyl-propyl)-4-piperidyl!-sulfonic acid amides and salts thereof
JPS5924971B2 (ja)	1984-06-13	新規なアミン類の製造方法
FI89909B (fi)	1993-08-31	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara sulfonamidderivat och mellanprodukter
US3928358A (en)	1975-12-23	Piperazine derivatives
IE48073B1 (en)	1984-09-19	Substituted 2-phenylimino-imidazolidines
EP0002886B1 (en)	1981-10-14	Indole derivatives, their preparation and use in pharmaceutical compositions
US3998953A (en)	1976-12-21	1,3,7-Trisubstitued xanthine peripheral vasodilators
US4031219A (en)	1977-06-21	Bis-homophthalimides and salts thereof
JPS5846516B2 (ja)	1983-10-17	置換トリフルオロエチルアミン
NO155056B (no)	1986-10-27	Sprengstoff.
EP0080992B1 (en)	1987-07-15	1-piperazinocarboxylates, process for their preparation and pharmaceutical compositions containing them
US4699910A (en)	1987-10-13	N-(3-trifluoromethyl-phenyl)-N'-propargyl-piperazine and salts thereof useful as analgesics
JPH01131150A (ja)	1989-05-24	エタノールアミン誘導体
AU597727B2 (en)	1990-06-07	Aryloxy-aminoalkanes
US4000313A (en)	1976-12-28	1-Isopropylamino-3[4'-(2-methoxy- or ethoxy-carbonylaminoethoxy)-phenoxy]propanol-2 and cardioselective antagonism use
JPS6218543B2 (es)	1987-04-23